# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 2108430'
loop_
_audit_author_name
_audit_author_address
'Gen-Qiang Chen'
;Southern university of science and technology
China
;
_audit_update_record             
;
2021-09-08 deposited with the CCDC.	2022-02-03 downloaded from the CCDC.
;
_audit_creation_date             2021-09-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H18 N2 O2'
_chemical_formula_sum            'C14 H18 N2 O2'
_chemical_formula_weight         246.30
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.5260(7)
_cell_length_b                   7.7633(6)
_cell_length_c                   9.5887(8)
_cell_angle_alpha                90
_cell_angle_beta                 98.910(3)
_cell_angle_gamma                90
_cell_volume                     627.02(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9535
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.675
_cell_measurement_theta_min      4.668
_shelx_estimated_absorpt_T_max   0.932
_shelx_estimated_absorpt_T_min   0.913
_exptl_absorpt_coefficient_mu    0.710
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.4687
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1546 before and 0.0936 after correction. The Ratio of minimum to maximum transmission is 0.6219. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            17968
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.625
_diffrn_reflns_theta_min         4.668
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.838
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.971
_reflns_number_gt                2445
_reflns_number_total             2463
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 1100 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2463
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0331
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0490P)²+0.1191P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0858
_refine_ls_wR_factor_ref         0.0859
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9a,H9b), C10(H10a,H10b), C11(H11a,H11b), C13(H13a,H13b)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
2.d Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.68084(17) 0.20951(18) 0.24487(16) 0.0253(3) Uani 1 1 d . . . . .
O2 O 0.46162(16) 0.36949(19) 0.16931(15) 0.0226(3) Uani 1 1 d . . . . .
N1 N 0.83573(19) 0.8897(2) 0.38390(18) 0.0198(4) Uani 1 1 d . . . . .
H1 H 0.780(3) 0.979(4) 0.345(3) 0.032(7) Uiso 1 1 d . . . . .
N2 N 0.60139(19) 0.4251(2) 0.38139(17) 0.0192(4) Uani 1 1 d . . . . .
C1 C 0.9189(2) 0.7950(2) 0.2953(2) 0.0187(4) Uani 1 1 d . . . . .
C2 C 0.9948(2) 0.8550(3) 0.1859(2) 0.0236(4) Uani 1 1 d . . . . .
H2 H 0.989885 0.973080 0.159593 0.028 Uiso 1 1 calc R . . . .
C3 C 1.0780(2) 0.7362(3) 0.1164(2) 0.0259(4) Uani 1 1 d . . . . .
H3 H 1.130818 0.774359 0.041718 0.031 Uiso 1 1 calc R . . . .
C4 C 1.0852(2) 0.5625(3) 0.1542(2) 0.0248(5) Uani 1 1 d . . . . .
H4 H 1.142832 0.483921 0.105525 0.030 Uiso 1 1 calc R . . . .
C5 C 1.0080(2) 0.5039(3) 0.2634(2) 0.0216(4) Uani 1 1 d . . . . .
H5 H 1.012509 0.385735 0.289369 0.026 Uiso 1 1 calc R . . . .
C6 C 0.9248(2) 0.6200(2) 0.3332(2) 0.0181(4) Uani 1 1 d . . . . .
C7 C 0.8414(2) 0.6017(2) 0.4611(2) 0.0175(4) Uani 1 1 d . . . . .
H7 H 0.923330 0.615555 0.546999 0.021 Uiso 1 1 calc R . . . .
C8 C 0.7368(2) 0.7656(2) 0.4473(2) 0.0191(4) Uani 1 1 d . . . . .
H8 H 0.718965 0.806269 0.542593 0.023 Uiso 1 1 calc R . . . .
C9 C 0.7523(2) 0.4333(3) 0.4775(2) 0.0195(4) Uani 1 1 d . . . . .
H9A H 0.819625 0.334811 0.458554 0.023 Uiso 1 1 calc R . . . .
H9B H 0.731716 0.423302 0.575978 0.023 Uiso 1 1 calc R . . . .
C10 C 0.5774(2) 0.7355(2) 0.3513(2) 0.0185(4) Uani 1 1 d . . . . .
H10A H 0.506856 0.835496 0.357929 0.022 Uiso 1 1 calc R . . . .
H10B H 0.595498 0.725546 0.252153 0.022 Uiso 1 1 calc R . . . .
C11 C 0.4968(2) 0.5727(2) 0.3930(2) 0.0192(4) Uani 1 1 d . . . . .
H11A H 0.475265 0.583090 0.491165 0.023 Uiso 1 1 calc R . . . .
H11B H 0.394445 0.556017 0.330056 0.023 Uiso 1 1 calc R . . . .
C12 C 0.5895(2) 0.3253(2) 0.2639(2) 0.0191(4) Uani 1 1 d . . . . .
C13 C 0.4270(2) 0.2625(3) 0.0439(2) 0.0246(4) Uani 1 1 d . . . . .
H13A H 0.527679 0.221277 0.016262 0.030 Uiso 1 1 calc R . . . .
H13B H 0.370610 0.331860 -0.034893 0.030 Uiso 1 1 calc R . . . .
C14 C 0.3262(3) 0.1104(3) 0.0705(3) 0.0310(5) Uani 1 1 d . . . . .
H14A H 0.293762 0.047974 -0.018157 0.047 Uiso 1 1 calc GR . . . .
H14B H 0.231701 0.150692 0.107336 0.047 Uiso 1 1 calc GR . . . .
H14C H 0.387503 0.033452 0.139445 0.047 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C12 1.221(2) . ?
O2 C12 1.350(2) . ?
O2 C13 1.453(2) . ?
N1 H1 0.89(3) . ?
N1 C1 1.397(3) . ?
N1 C8 1.472(2) . ?
N2 C9 1.463(2) . ?
N2 C11 1.467(2) . ?
N2 C12 1.358(3) . ?
C1 C2 1.394(3) . ?
C1 C6 1.405(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.395(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.395(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.397(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.382(3) . ?
C6 C7 1.516(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.548(3) . ?
C7 C9 1.532(3) . ?
C8 H8 1.0000 . ?
C8 C10 1.537(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.520(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.505(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O2 C13 116.73(16) . . ?
C1 N1 H1 116.2(18) . . ?
C1 N1 C8 106.51(15) . . ?
C8 N1 H1 112.3(18) . . ?
C9 N2 C11 113.78(15) . . ?
C12 N2 C9 119.53(16) . . ?
C12 N2 C11 122.72(16) . . ?
N1 C1 C6 110.63(17) . . ?
C2 C1 N1 128.31(19) . . ?
C2 C1 C6 121.01(19) . . ?
C1 C2 H2 121.0 . . ?
C1 C2 C3 117.9(2) . . ?
C3 C2 H2 121.0 . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.32(19) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.18(19) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.4 . . ?
C6 C5 C4 119.17(19) . . ?
C6 C5 H5 120.4 . . ?
C1 C6 C7 107.31(17) . . ?
C5 C6 C1 120.37(18) . . ?
C5 C6 C7 132.10(18) . . ?
C6 C7 H7 107.5 . . ?
C6 C7 C8 100.97(15) . . ?
C6 C7 C9 117.73(16) . . ?
C8 C7 H7 107.5 . . ?
C9 C7 H7 107.5 . . ?
C9 C7 C8 114.94(15) . . ?
N1 C8 C7 102.35(15) . . ?
N1 C8 H8 110.4 . . ?
N1 C8 C10 111.24(15) . . ?
C7 C8 H8 110.4 . . ?
C10 C8 C7 111.72(15) . . ?
C10 C8 H8 110.4 . . ?
N2 C9 C7 112.00(15) . . ?
N2 C9 H9A 109.2 . . ?
N2 C9 H9B 109.2 . . ?
C7 C9 H9A 109.2 . . ?
C7 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C8 C10 H10A 109.4 . . ?
C8 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C11 C10 C8 111.27(15) . . ?
C11 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
N2 C11 C10 108.97(14) . . ?
N2 C11 H11A 109.9 . . ?
N2 C11 H11B 109.9 . . ?
C10 C11 H11A 109.9 . . ?
C10 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?
O1 C12 O2 123.64(18) . . ?
O1 C12 N2 125.19(18) . . ?
O2 C12 N2 111.16(16) . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
O2 C13 C14 110.91(17) . . ?
H13A C13 H13B 108.0 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
